Friends for Hire — Do You Need an Entourage?

When it comes to an entourage, where does one draw the line between paid professional and trusted confidant? Erin Flaherty rolls with a full-time beauty crew to find out.

What would you do with a celebrity entourage?
(Image credit: Peter Yang)

By now we all know hairstylists make the next-best dates - J.Lo leaned on Oribe through several rocky romances; ditto for Jessica Simpson and her beloved Ken Paves. What is it about beauty experts that encourages such intimacy? Would living with an entourage be fabulously empowering or just a paparazzi-like invasion of privacy? To find out, Marie Claire fixed me up with my own full-time support crew, at my disposal for four days - the average length of a celeb press junket.

I start at New York's chichi Four Seasons Hotel, base camp for the duration of the experiment. My sprawling suite is definitely star-caliber (ahem, two bathrooms and a walk-in closet — the equivalent of the Taj Mahal in cramped Manhattan), and I'm about to kick back and admire the view when the bell rings. Danilo — just Danilo — my hairstylist, is here with a trunkful of tools and Pantene products (he's the brand's spokesperson). Danilo's a little intimidating: tall and blond with amazing kohl-rimmed eyes, a go-to guy for countless A-listers (longtime client Gwen Stefani is a close friend). Trailing him is CND backstage nail guru Angi Wingle, a laid-back Texan. And next, sweet Kate Winslet look-alike Kate Lee, my makeup artist, arrives. She works with Chanel and has done famous people like the aforementioned Ms. Winslet, Keira Knightley, and now, um, me. Suddenly, all three attack me with brushes, irons, and files, and I can't help feeling like the dorky girl who gets transformed into a princess in some lame teen flick.

I'm not the chattiest Cathy, but I feel the pressure to be "on" while all this unfolds. And once I initiate conversation, the environment turns from mildly awkward to old-fashioned beauty parlor. I want to understand the ground rules. How are these grooming gurus paid? When you spot Jennifer Aniston having coffee with Chris McMillan in Us Weekly, is he on the clock? I learn it's usually the studios and record companies that pick up the fees. (Remember the alleged $10,000-a-day demands of J.Lo's hair and makeup crew? You think she sprang for that?) And for the most part, strictly social outings - even if they do involve some preening — are pro bono. As Kate puts it, "You don't become a celebrity go-to unless there's a genuine connection between you and your client."

With that in mind, I decide to spend the afternoon hanging with "my people," and Danilo suggests a bonding session at his place. His posh, recently remodeled apartment is stuffed with photographs from his world travels with the rich and famous, slightly different from my tiny pad. But the fact that my hairstylist is eminently more fabulous than I am just heightens his appeal. I feel especially close to him when he only half-jokingly invites me to road test his new Japanese-style bidet.

Perhaps sensing our budding chemistry, Kate and Angi vie for my attention by sharing their most ridiculous on-the-job requests. "Oh gawd," Kate moans in her lilting British accent. "I've had to get on my knees and trim someone's pubic hair so she could go pantyless in a dress." Sheesh! After a few hours together, I feel like spilling the most intimate details about my sex life and have to remind myself that we've only just met. I begin to understand why these pros are worth every cent: Along with providing spritzes and polish and touch-ups, they shower me with genuine (I think) compliments and encouragement. Filled with possibly false confidence, I want to parade around the city in hopes of running into every ex I've ever had. My team advises me otherwise, and we call it a night.

The next morning, we hit Equinox Fitness for a session with Kacy Duke, personal trainer to, oh, Julianne Moore and Denzel Washington. And since Danilo frequently works out with Gwen, I invite him to do the same with me. When my group enters the gym, everyone is staring. If you're ever pining for attention, don sunglasses, a baseball cap, and red lipstick and ask a bunch of friends to walk ever so slightly in front of you. A girl gawks at me and whispers loudly to her friend, "Who is that?" and I have to admit, I feel more, well, important than usual. On the other hand, I'm full of dread — I haven't broken a sweat since last summer.

What would you do with a celebrity entourage?

(Image credit: Peter Yang)

Luckily, Kacy's not a barking drill sergeant; she's a warm, petite yet strong-looking woman who greets me with, "So what's your sign?" Having Danilo as my workout buddy further eases my pain — we're equally breathless after a cardio romp and laugh through stretches. It's added motivation for me (plus, he tweaks my ponytail when it starts to droop), a free workout for him. Everyone wins.

Afterward, we head to the tony Cafe Cluny for a meeting with the very cool Esther Blum, author of Eat, Drink, and Be Gorgeous, yet another specialist tasked with increasing my fabulousness this week. Over fresh grilled trout, Esther fires off nutrition tips, suggesting that I omit bread, cheese, and wine for a month (help!). Unsympathetic, my crew is busy drilling her about their own diet dramas. Hello?! If I were Nicole Kidman, would they quietly act fascinated by my love of smoked gouda? It's the first time I'm slightly annoyed by, well, rolling so deep.

As much as the constant companionship is comforting, it's nice to retire to the hotel that night. For a moment in the shower, I almost expect a handmaiden to pass me a towel, which is when I realize how spoiled I've become. Then, Danilo's tip to do a hair mask echoes in my head. Can I get some privacy here, people? Greta Garbo's famous expression comes to mind: "I vant to be alooonnnee!"

On Friday night, we all head to the impossibly chic Italian enoteca Il Posto Accanto. My boyfriend, Shya, joins us and can't stop staring at my dramatically made-up face. I briefly wonder if I resemble Dame Edna, but instead he floors me with, "You look gorgeous!" Obviously, I want to continue this scintillating conversation, but I feel compelled to interact with my group. Being the center of attention is exhausting: What if Danilo and Kate got into an argument? I'd have to mediate, maybe even choose a side. Angi is more the quiet type — does she ever feel overshadowed? Luckily, as I survey the table of happy diners, the only place this drama is playing out is in my neurotic head. A few glasses of pinot grigio lifts the pressure, but somehow it's all bittersweet. Tomorrow, Danilo is booked with Rufus Wainwright (a real client), Angi heads home to Pennsylvania, and Kate catches a p.m. flight to L.A. to tend to Juno's Ellen Page. I, on the other hand, feel like my coach is about to turn back into a pumpkin and am afraid my newfound confidence will disappear with it. Could this be how Jessica feels when Ken gets called away by Eva Longoria?

The next morning, I have a wine-fueled headache and a puffy face, but dear Kate's still there to transform me with her arsenal of eyeliners. Then Esther shows up and offers me a nutritious Perricone PEP drink, and Shya marvels, "Celebrities can pay people to handle their hangovers?" This strikes a chord. Do famous people act irrationally because they have so many buffers to keep them protected from, you know, reality? Six more months of this and I could see myself demanding only white M&Ms in my dressing room.

My two remaining shadows join Shya and me for a final outing to Whole Foods. I miss Danilo and Angi terribly (and fret over my self-styled hair). I'm about to have a full-on diva meltdown when a store employee approaches us huddled around Esther's cart and says, "Can you please move along? You're causing a traffic jam." Just as I decide to let him have it, I "take five," notice the crowd trying to pass us, and concede that traveling in a herd can be just as bothersome as it is beneficial. As Shya and I head out of the store alone, I conclude that two may be company, but six is definitely a crowd.